Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★

Acta Chimica Sinica, Год журнала: 2023, Номер 81(7), С. 793 - 793

Опубликована: Янв. 1, 2023

o-Hydroxyphenyl substituted p-quinone methides (p-QMs) belong to a class of p-QMs with unique advantages.They not only maintain the high reactivity p-QMs, but also have more reactive and activation sites owing introduction hydroxyl group.Therefore, o-hydroxyphenyl wide applications in synthetic medicinal chemistry.The catalytic asymmetric 1,6-conjugate addition [4＋n] cycloaddition developed very rapidly recent years, which become efficient strategies for synthesis chiral oxygen-containing heterocycles arylmethanes potential bioactivity.This review summarizes reactions involving points out remaining challenges this research area, will open new window design type their involved reactions.

Язык: Английский

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Organocatalytic Enantioselective 1,12‐Addition of Alkynyl Biphenyl Quinone Methides Formed In Situ

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(29)

Опубликована: Май 3, 2024

The chemistry of quinone methides formed in situ has been flourishing recent years. In sharp contrast, the development and utilization biphenyl are rare. this study, we achieved a remote stereocontrolled 1,12-conjugate addition for first time. presence suitable chiral phosphoric acid, alkynyl were generated from α-[4-(4-hydroxyphenyl)phenyl]propargyl alcohols, followed by enantioselective with indole-2-carboxylates. strategy enabled alcohols to serve as efficient allenylation reagents, providing practical access broad range axially allenes bearing (1,1'-biphenyl)-4-ol unit, which previously less accessible. Combined control experiments, density functional theory calculations shed light on reaction mechanism, indicating that enantioselectivity originates nucleophilic methides. Notably, not only versatile intermediates was confirmed but also organocatalytic 1,12-addition established.

Язык: Английский

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Organocatalytic Asymmetric Conjugate Addition of Fluorooxindoles to Quinone Methides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6100 - 6105

Опубликована: Апрель 15, 2024

Fluorooxindoles undergo asymmetric Michael addition to para-quinone methides under phase-transfer conditions with 10 mol% of a readily available cinchona alkaloid ammonium catalyst. This reaction affords sterically encumbered, multifunctional fluorinated organic compounds displaying two adjacent chirality centers high yields, ee's and dr's.

Язык: Английский

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Palladium-Catalyzed Asymmetric (2+3) Annulation of p-Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p-Dienones

Organic Letters, Год журнала: 2020, Номер 22(11), С. 4171 - 4175

Опубликована: Май 20, 2020

A novel asymmetric catalytic (2+3) annulation of p-quinone methides with CN-substituted trimethylenemethane is described under palladium catalysis, providing an alternative approach for the enantioselective construction highly functionalized chiral spirocyclopentyl p-dienones. Driven by significant improvement in reactivity and enantioselectivity, a type non-C2-symmetric phosphoramidite ligand from chirality-matched combination (S)-BINOL sterically demanding amine derived l-hydroxyproline evolved explored protocol presented here.

Язык: Английский

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Organocatalytic site- and stereoselective 1,6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(21), С. 3446 - 3451

Опубликована: Янв. 1, 2020

A chiral phosphoric acid catalyzed site-selective 1,6-conjugate addition of N-aryl-3-oxobutanamides to in situ formed propargylic aza-p-quinone methides from alcohols has been established for the first time.

Язык: Английский

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